Diisopropylamine → HCID 13655521, compound

Participants

Reaction Conditions

Reaction Steps

To a 3-neck, 250-ml flask equipped with an addition funnel, argon inlet and a septum were added 25 mls of anhydrous tetrahydrofuran and 5.7 mls of diisopropylamine (passed through activity I neutral alumina) under an argon atmosphere. The system was cooled to about 0° C. and 33 mls of 1.6M butyl lithium solution (in hexane) were then added via a syringe. The system was stirred at 0° C. for 5 minutes and then further cooled to -68° C. After cooling, 6.1 gms of 1-cyano-1-(1,2,4-triazol-1-yl)ethane in tetrahydrofuran were added to the system. The system was stirred at -68° C. for 1 hour and then 8.8 gms of 2,4-dichlorobenzaldehyde were slowly added to the system. The system was allowed to warm to room temperature over 30 minutes. Saturated aqueous ammonium chloride was then added to the system and the product was extracted with methylene chloride. The organic solution was washed with water, dried over sodium sulfate and filtered. The solvent was removed by stripping to yield a yellow oil. This oil was then taken up in diethyl ether resulting in the precipitation of 4.1 gms of the erythio isomer of the title compound. The mother liquors were concentrated and again taken up in diethyl ether resulting in the precipitation of 2.60 gms of the threo isomer of the title compound, m.p. 164° -168° C.

Provenance & Evidence